Synthesis and biological actions of highly potent and prolonged acting biotin-labeled melanotropins

Dhirendra N. Chaturvedi, James J. Knittel, Victor J. Hruby, Ana Maria de L. Castrucci, Mac E. Hadley

Research output: Contribution to journalArticle

38 Scopus citations

Abstract

Biocytin derivatives of a superpotent analogue of α-melanotropin, [Nle4,D-Phe7]-α-MSH, were prepared. [Naα-Bct-Ser1,Nle4,D-Phe7]-α-MSH and [12-Bct-Nα-dodecanoyl-Ser1,Nle4,D-Phe7]-α-MSH were synthesized by solid-phase techniques, and the coupling of biotin and 12-aminododecanoic acid was achieved through their succinimido esters. These melanotropins possessed almost identical actions to [Nle4,D-Phe7]-α-MSH as determined by several melanocyte bioassays. Both biocytin derivatives were highly potent agonists and exhibited prolonged biological activity as determined in the frog and lizard skin bioassays. Both biotinylated peptides were at least equipotent to α-MSH in stimulating Cloudman S91 mouse melanoma tyrosinase activity. The analogues were resistant to inactivation by α-chymotrypsin.

Original languageEnglish (US)
Pages (from-to)1406-1410
Number of pages5
JournalJournal of Medicinal Chemistry
Volume27
Issue number11
DOIs
StatePublished - Mar 1984

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery

Fingerprint Dive into the research topics of 'Synthesis and biological actions of highly potent and prolonged acting biotin-labeled melanotropins'. Together they form a unique fingerprint.

  • Cite this